Processes To Separate Enantiomers

Lorenz, Heike; Seidel‐Morgenstern, Andreas

doi:10.1002/anie.201302823

Cited by 424 publications

(394 citation statements)

References 277 publications

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“…However, such highly purified product is hard to obtain from a multi-component solution by direct crystallization, such as the product stream from a type-I Multicomponent Reaction (MCR), [5,6] or a racemic mixture of chiral pharmaceutical compounds, [7] since a mixed suspension is a likely result. Further purification of the solid phase usually requires additional steps (see Figure 1 (a) for instance), which will inevitably lead to the loss of valuable products.…”

Section: Concomitant Solid Separation Through Electric Field Enhancedmentioning

confidence: 99%

Solid Separation from a Mixed Suspension through Electric‐Field‐Enhanced Crystallization

Radacsi

Kramer

et al. 2016

Angew Chem Int Ed

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This version is available at https://strathprints.strath.ac.uk/59326/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. COMMUNICATION Concomitant Solid Separation through Electric Field Enhanced CrystallizationWei W. Li, [b] Norbert Radacsi, [b] Herman J.M. Kramer, [b] Antoine E. D. M. van der Heijden [b] and Joop H. ter Horst* [a] Abstract: When applied to a pure component suspension in an apolar solvent, a strong inhomogeneous electric field induces particle movement and the particles are collected at the surface of one of the two electrodes. This new phenomenon was used to separately isolate two organic crystalline compounds, phenazine and caffeine, from their suspension of 1,4-dioxane. First, the crystals of both compounds were collected at different electrodes under the influence of the electric field. Subsequent cooling crystallization allowed the immobilization and growth of the particles on the electrodes, which were separately collected after the experiment with purities higher than 91%. This method can be further developed into a technique for crystal separation and recovery in complex multicomponent suspensions of industrial processes.Crystallization is an effective and efficient separation technology that can, in a single process step, recover the desired compounds from solutions as high purity (>99%) crystalline solids [1,2,3,4] . However, such highly purified product is hard to obtain from a multi-component solution by direct crystallization, such as the product stream from a type-I Multicomponent Reaction (MCR), [5,6] or a racemic mixture of chiral pharmaceutical compounds, [7] since a mixed suspension is a likely result. Further purification of the solid phase usually requires additional steps (see Figure 1 (a) for instance), which will inevitably lead to the loss of valuable products. Alternatively, a single crystallization step coupled with simultaneous particle separation could diminish the product loss wh...

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Section: Concomitant Solid Separation Through Electric Field Enhancedmentioning

confidence: 99%

Solid Separation from a Mixed Suspension through Electric‐Field‐Enhanced Crystallization

Radacsi

Kramer

et al. 2016

Angew Chem Int Ed

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“…The use of dielectric properties of solvents to influence resolutions is particularly interesting [25,26]. Excellent practical hints have been given [27], and a wide ranging very recent review of all processes to separate enantiomers is available [28].…”

Section: Diastereomeric Resolutionsmentioning

confidence: 99%

How to Use Pasteur’s Tweezers

Kellogg

2015

Advances in Organic Crystal Chemistry

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Pasteur introduced two techniques to separate enantiomers. The common visual imagery is that of the first technique, which pertains to the use of tweezers to separate the mirror image crystals of a tartaric acid salt. A second method discovered thereafter, not restricted to the conglomerates necessary for the tweezer approach, is diastereomeric resolution. In this chapter, a short discussion is given of the basic principles of diastereomeric resolutions followed by short analysis of Dutch Resolution, a method based on the use of families of resolving agents. The role of specific nucleation inhibition is discussed. Attention is then turned to conglomerates. Preferential crystallisation is discussed briefly. Particular attention is paid to the discovery of near-equilibrium methods to separate (racemisable) conglomerates by employment of constant attrition of the growing crystals. This methodology has been extended to preparation of the chiral components of some major drugs, and the methodology has also been adapted to separation of nonracemisable conglomerates.

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“…2 Since pioneering Pasteur's experiments and till the present time, comprehensive research on chiral compounds has greatly succeeded in understanding their phase behaviour and crystal structure [3][4][5] and applying crystallization processes for resolution of racemates. 6 Nevertheless, a complete theory of solid solution formation has not been elaborated yet. 7 One of the obvious reasons for this is the difficulty in identifying and studying the scarce partial [8][9][10][11][12][13][14] and continuous [15][16][17][18][19][20][21][22][23] solid solutions of enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Structural aspects of partial solid solution formation: two crystalline modifications of a chiral derivative of 1,5-dihydro-2H-pyrrol-2-one under consideration

et al. 2017

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The purposeful change of crystallization conditions for rac-3-chloro-5-hydroxy-1-(4-methylbenzyl)-4-[(4-methylphenyl)sulfanyl]-1,5-dihydro-2H-pyrrol-2-one 1 leads to two different crystal modifications, namely, a racemic compound in the triclinic space group P1 with Z′ = 1 (α-1) and a partial solid solution based on a racemic compound in the monoclinic space group P2 1 with Z′ = 4 (β-1). The first modification, α-1, is characterized by a higher density of the molecular packing in the crystal, while the second one, β-1, by a stronger system of hydrogen bonds and the presence of positional and substitutional disorder simultaneously.The analysis of the crystal structure of modifications α and β allowed us to define some structural aspects of the partial solid solution formation. Namely, the tendency to build a stronger hydrogen bond system enables the solution of enantiomers of 1 to be formed in the crystalline phase, whereas the propensity of the molecules to adopt a more favorable transoid conformation limits the solubility of the minor enantiomer.

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Processes To Separate Enantiomers

Cited by 424 publications

References 277 publications

Solid Separation from a Mixed Suspension through Electric‐Field‐Enhanced Crystallization

Solid Separation from a Mixed Suspension through Electric‐Field‐Enhanced Crystallization

How to Use Pasteur’s Tweezers

Structural aspects of partial solid solution formation: two crystalline modifications of a chiral derivative of 1,5-dihydro-2H-pyrrol-2-one under consideration

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